All characters depicted are 18+. This story contains the following themes: bondage, feminization, sissies, spanking, and other kink-related content.

A few hours prior to Maid Madeline being caught...

"Cha-ching!" Some office staff turned around to see Mario fist-pumping at his desk. Amy, one of the interns, had just forwarded him a slew of information on what seemed to his biggest catch yet. According to her, there was a new establishment opening deep in the woods well away from prying eyes.

Normally this might be semi-scandalous with some sort of brothel or private club opening for guys to get away with some dirty stuff. But according to Amy, this place catered to sissies.

He was fascinated reading through all the information she'd gathered. Guys were actually paying to be dressed and locked up in frilly maid's outfits! Not only that, but they were made to cook and clean for the proprietor of this establishment, whose name was kept off all records they could scrounge up. Some of them even got punished for their work and enjoyed it!

Playing with a stress ball, Mario leaned back and evaluated the situation. If this was real...what could he do? Normally, he'd dress up nicely, get reimbursed for a tuxedo or suit, and try to get one of the “girls” by herself and interview her under a confidentiality clause.

In this case, there didn't seem to be guys going in and out unless they were all frilled up. He could try to question one of the patrons, but he doubted they would want to admit to doing any of this. Stumped, he called in Amy to confirm some information.

"So how did you come across all this info anyhow? This isn't some sort of prank, is it?" asked Mario with narrowed eyes.

"Oh no, I would never Mr. Mario! I respect you too much for that. No, I actually caught my roommate coming in late one night. He seemed real skittish, so I asked him what's up. He started acting cagey, so I started teasing him and tried to grab his bag. He dropped it by accident and all these clothes started pouring out!” Amy liked to talk with her hands, it made for a fun show.

“Like a big floofy maid uniform, a big ole wig, some gaudy heels...anyway, I started putting pressure on him. He admitted that he was stressed and started going to this sissy club out in the woods. Apparently, a bunch of men go out there to relieve stress, but the big thing is he says he recognizes some big people! He mentioned the mayor. I couldn't get anything else out of him, but what cha think?! Is this a big story or what?"

Amy gushed all this information onto Mario in a flurry of words. This was enough to convince him to investigate. She was too much of a ditz to lie. If he could catch some big names, like say the mayor, teetering around in heels and skirts, oh boy. He'd be up for Journalist of the Year!

"Alright, that's good enough for me. Re-send that info to my private email, I want to keep off the books for this one. I think I have an idea of how to get in and will need your help..." Amy was bursting with excitement as Mario told her what they would need to do to get into this place.

"Maybe Journalist of the Year isn't worth it after all..." pondered Mario as he stared at the ensemble laid before him.

Amy had gone home and, after promising her roommate that she wouldn't tell any of their friends, borrowed his sissy maid outfit. The light pink outfit was frilly alright, with a skirt that would barely cover his pantied ass. Combined with the fishnets and high heels, he was feeling incredibly nervous about this investigation.

Underneath this all, he'd be wearing the equivalent of a skimpy, pink negligee which doubled as a tight corset. "Ok. You're sure you can do my makeup right?"

"Oh of course!" said Amy as she began pulling out various powders and tubes. "I can get you all done up like a proper sissy Mr. Mario, don't you worry. Now go ahead and get dressed, don't forget the breastplate before I tie your corset. Then we can glue your wig on! Otherwise, that massive thing is gonna fall off!"

Mario sighed as he got to work putting everything on, glad that his last investigation involved a waxing salon that was overcharging customers. Amy found him the oddest stories, but they always had a great payoff.

The huge breastplate and silicon hip pads really helped to fill out his figure, which got painfully better as Amy cinched his waist. He heard a click as she made a few finishing touches on his accessories, realizing that she was locking him up! "Amy, what the hell are you doing?!"

"Oh, don't worry your cute booty Mr. Mario. My roomie had these all over his dress too, it's one of the conditions to be dressed properly for this place y'know," she explained, placing a wig cap on his head. "Now this is going to feel weird, but you have to glue this wig on for it to stay in place."

The glue indeed felt oddly cool as she slathered it under the seams of his wig cap. The bright, fuchsia wig weighed a ton as it was placed upon his head, straining his neck muscles. The bouffant wig looked and felt as voluminous as the dress itself!

"Alright Mr. Mario, you're as done up as any sissy could be! Go knock 'em dead. Or investigate! Investigatin' is what you're doing," laughed Amy as she pushed him out of the car towards the mansion.

They'd parked the car a good bit away from the entry gates, much to Mario’s regret. It felt like miles as Mario teetered on his heels towards the doors. He craned his neck around as much as possible, trying not to get distracted by the swaying of his gigantic breasts or the breeze on his mostly bare ass.

He'd placed one of his tiny cameras into the choker he'd been given, making sure to get as much footage as possible. He'd have to remember to delete any footage of himself getting ready…or else the staff would see it. He'd also owe Amy big time, not just for helping him with the investigation, scoop, and disguise...but also to keep her mouth shut about the whole thing.

As he made his way through the front gates and door unhindered, he stared in awe at the inside of this mansion. It bled extravagance, with several priceless-looking vases and ornaments adorning the walls, pedestals, and ceiling.

He also got an eyeful of sissy booty and chests as he passed several maids all focused on cleaning various parts of the house. It was so odd, were they having fun just being dressed up and put to work? If there were bigwigs here paying to be used as bad labor...there had to be something else going on...

As Mario pondered the situation, he got a glimpse inside a room with the door halfway open. Inside was what he was looking for! He saw several crops, paddles, and other tools of bondage lining the walls, with several devious looking devices crowding the floor.

Peeking in, he also saw..."Oh my god...it's the friggin' mayor!" Even with the mayor looking like a tart in his maid uniform, Mario would recognize that jawline and mole anywhere. As a final piece of evidence, he also caught sight of the mayor's rumored heart tattoo on his right butt cheek. This was exactly what he needed, now to get out of here without getting caught...

Mario backed up, trying not to make too much noise as his heels clacked against the stone floor. Unfortunately, his rustling skirts brushed up against one of the many priceless-looking vases sitting on a pedestal right behind him.

His stomach dropped as he heard the porcelain crash to the floor and a following dreadful silence. He turned around to see many of the maids looking at him with their hands over their mouths and others looking somewhat...jealous?

"Well, well, well. Looks like someone couldn't wait to get their turn in the punishment room. You know the deal, you can get ahead if you misbehave, but you have to cover double the cost of anything you break or destroy to get there. Tsk tsk, looks like you went and broke my favorite vase too, that one will cost you several hundred thousand I'm afraid. Hmm, what's your name sissy?"

A tall, imposing woman stood over Mario. Her hair was tied back in a tight bun, and she wore a tight leather skirt with a cream colored silk blouse. There was something familiar about her face, but he couldn't quite focus on it. Mario gulped as he noticed her tapping a large, heart-shaped crop against her leg.

He needed to get out of here somehow, he didn't have that kind of money! But there was no way he could run without breaking his ankles in these heels.

"Uh um, I'm Maria…m-ma'am," squeaked Mario, attempting to curtsey in front of her.

"Hmm, Maid Maria? I don't recall having a Maria...ahh, actually now I do recall having a Maria coming in. Yes. Well, sissy girl, let's get you ready for your punishment." Grabbing Maria's arm, the mistress pulled him forward and into the punishment room.

Maria's heart was beating fast, he had to find a way out of this situation. Whoever this other Maria was, he could deal with the price of the vase instead! Unfortunately, he was distracted by the sight of several other sissy maids lining the other wall of this room, each of them holding their skirts up, displaying reddened behinds.

As he was running through scenarios in his head to escape, he felt something behind his back and then his maid's dress fell to the floor. Looking down, he was left in his silky negligee and corset. Confused, he tried to turn around but felt a firm hand pushing his head forward.

"Now, now Maid Maria. You know the drill, don't you? I want you to count to 20 and each time I want you to say, 'I'm Maria and I'm a naughty sissy maid who deserves and wants to be punished', ok? Well?"

He flinched as he heard the smack of the crop hitting her hand. He realized there was no way out of this situation. If he made too big a show of getting out of here, surely one of these sissies would recognize him and out him as an investigative journalist.

He was sure he'd already outed some of these sissies for other things like minor embezzlement, fraud, or something. Gulping he realized his best way out was to go with the flow...

"O-one..AHH!" He cried as he felt the hard crack of the first smack. It was more painful than he imagined, realizing that the mistress has switched to a large paddle! "I-I'm Maid Maria and I-I'm a naughty sissy maid w-who deserves and w-w-wants to be punished...two, AHH!"

Every repetition was followed by the sound of a large object swishing then followed up with a yelp from Maria.

This continued for what seemed like forever, as tears ran down Maria's face and both his face and butt turned right red. As the mistress finished and lined him up with the other sissies, he heard another commotion at the door. Trying to distract himself from the pain on his behind, he chanced a glance at the door.

"Ma'am, I found a curious sissy spying in the doorway. You'll be interested to know that she is slightly different than the other sissies," said another stern-looking woman. Maria thought the new sissy maid in tow looked a bit odd compared to the other sissies...before realizing that she was no sissy!

"Madeline?! What the hell is she doing here? This is my scoop!" hissed Maria to himself. His mood shifted after a brief moment. He couldn't help but smirk to as Maid Madeline was made to go through the same routine as himself before being lined up next to him.

"Hey! Why are you here? I got dibs on this story Maddie, I didn't dress up like some sissy tart just to share the credit!" whispered Maria to Madeline.

"Well, your interns should do a better job of keeping secrets. Plus, I didn't want to dress up like this either! Look you're not in a great position to negotiate name order on this story, so let's work together and get out of-" Madeline was cut off a loud cough from behind.

Both the sissy maids yelped as they felt their arms clamp behind their backs as they were put into some sort of restraining device. They felt the sharp tug of something else being attached to said devices. They each felt a quick slap to their exposed asses, confusing them in how quickly everything was applied!

"Quiet sissies. Hmm. I think I need both of you to follow me into my office. Quickly now!" The mistress beckoned them to follow.

Looking at each other, Maria and Maddie hesitated before being pulled by the stern-looking woman, who had leashes tied to their arm binders. Unable to escape, they both minced behind the woman towards a door at the end of a long hallway. The entire time, they heard whispers from the many sissy maids along the way, before they were shushed into silence.

Passing through the door, they were led into a splendidly furnished office. Sitting behind an ornate, walnut desk, the mistress beckoned for the sissies to sit. Before they had a chance to obey, or disobey, they were pushed down into chairs by another woman. The mistress pulled out a sheaf of papers and began rifling through them.

"Hmm, Maids Maria and Maddie, is it? Let me see where your contracts are...ahh, yes here we are. Mario and Madeline, is it?"

The two maids looked at one another terrified, how did they already have contracts here?!

"Yes, looks like you came by way of referral from a trusted employee of mine. Well, you haven't agreed to the terms and conditions yet but..." She gave a sinister smile to the two maids, who were now sweating.

"I'm sure we can come to an agreement sooner than later. Especially considering that you two are trespassing! Yes, I recognize you two. Even with those adorable outfits, you're clearly from that dreadful news network. Well, with your experience you must understand that trespassing on private property and a legal business to boot is...illegal. Not to mention that you've stolen services from me, expensive services I might add. Did you know that each of the sissies here pays $250,000 up front for the pleasure of serving me? Well, some of them get loaned that amount and pay it back with interest. Either way, you owe me now. In addition, Maria now owes $400,000. Maddie, you do realize that dress you're wearing is expensive as well? I'll say it's about the same."

Both Maddie and Maria gulped as the mistress smiled at them, realizing that they'd gotten themselves into a terrible situation. Neither of their salaries could cover the cost of their heels it seemed.

"Now, of course I'm willing to let you pay this debt off through hard work and you'll keep those dainty behinds of yours out of jail. As you can tell, I have several members of the local police department working for me as well. They wear blue dresses! Plus, to make sure you're properly punished, as that's part of the contract, I have something special in mind for you." The mistress pushed the contracts forward along with a pair of bright pink pens.

"W-wait, what do you mean we were referred here?" asked Maddie, trying to stall for time. At that moment, they all heard a knocking at the door. Turning around, the sissies saw none other than...

"Amy?! What the hell?" cried out Maria, as Amy the intern walked into the room and removed both chokers from around their necks. Maria was slapped on the behind in response to her outburst.

Realizing that they'd just lost their only chance of saving themselves, they watched with mouths agape as Amy walked around to sit on the desk next to the mistress. Both chokers were being handled gingerly. Amy sneered as she pecked a kiss on the mistress' cheek.

"Oh, I see you've met my daughter! Yes, she's been working long hours, unpaid I might add, at your news network. Hoping to get some experience in journalism but surprisingly, with you two dunces there she could never get a real position. So, now that you two are working as my maids, or going to jail. Your choice. Either way, she can finally move up in the world!"

Amy smiled at the two investigators, cheerfully adding, "Plus I even got a new apartment all to myself now that my roommate is sleeping here instead! I have to say Mr. Mario, I mean Maid Maria, it was real nice learnin' from you but if there's any lesson that was valuable...it's that sometimes you gotta step on a few people to get to the top! Just like you told me. Now, I also remember you telling me about your hidden camera techniques, so if you don't want select footage being broadcast from what you have saved here..."

The two maids shared one last glance, realizing they were trapped and sighed as they both struggled to sign their new contracts with their arms bound behind them.

A few weeks later...

Amy put her feet up on her new desk, increasing the volume on her office TV. Smiling, she was enjoying a glass of champagne as she watched her first story as an investigative journalist air.

"Good evening, we come to you tonight with breaking news! Investigator Amy broke ground with her first story on missing journalists Mario and Madeline. The two have not shown up for work for several weeks, but as we've come to find out, they have new positions outside of the news industry. That's right, the two former journalists are now the spokespeople for a booming new local business which is all the rage. S.M.S, or Sissy Maid Services, has been instrumental in getting our small city economy up and running again! The cheap service helps those in need get cleaned but with a smile and pretty frills. With their new ad, S.M.S. puts their top two maids front and center. Our network endorses this new business and we wish Maids Maria and Maddie the best!"

Amy laughed as she watched Maids Maria and Maddie do their best in advertising S.M.S. as the premier maid service in town. All while showing off their improved maid dresses and dancing to an upbeat tune. Their skirts and petticoats did nothing to hide their frilly panties or their obviously red behinds. A hallmark of all maids working for S.M.S.

She toasted the TV as the ad ended with the two making a heart shape with their arms and did their best to look like they were enjoying themselves. She made a mental note to pay a visit to her mom this weekend, making sure that she could be there for the two maid's weekly punishment.

She thought she could spice things up by bring a few special toys, still finding ways to help the 'motivation' of all the maids working under her mom. Maid Maria was constantly acting up, thinking he could talk his way out of punishments...but after being gagged with a feathered duster, it was much easier to get him to clean. Well harder to actually clean, he was quite clumsy and kept accumulating debt.

Maid Maddie on the other hand...Amy knew the woman never had a high opinion of her. So she was delighted to take a hand in shaping her mother's favorite new sissy. Making a man sing songs and chant about what what a sissy they are is fun...but making a woman do it? Oh, the mortified look on her face with every new shame and torture was incredible.

It had been especially fun when Amy had edited the footage from both their chokers to make it look as though they did everything willingly. Madeline's comment about how she hoped the girls at the office would never see this was especially useful in selling the footage to the network.

Amy smiled, pulling up her computer. She began working on other cases...after all, her mother needed new sissies every day and now she could essentially blackmail anyone she wanted.